Jacki's Journey into Sissyhood Pt. 05

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
jacki697
jacki697
363 Followers

"Lie down on your back," I ordered. He complied with my wishes, crawling on the bed and laying with his cock up. I picked up the lube from the table and lubed my hole, then added some to Curt's rod. I then straddled his prick and used my hands to guide it home. Curt's greased member easily slid into my waiting pussy, and I dug my fingers into his abdomen as I began to ride him. His cock felt amazing, as he rubbed my prostate as I bounced. My partner rocked his hips driving himself into me in sync with my hips. He was as adept at fucking as he was at dancing.

Curt then sat up and wrapped him muscular arms around my hips, and placing his lips on mine. We made out as I rode his erection. His mouth moved down my body, and began suckling at my tits. Curt's tongue danced with my nipples as his cock kissed my prostate. I wasn't long before I was screaming myself through an orgasm. I came hard, while riding his dick.

Not wanting the joy to end, I rotated myself into a reverse cowgirl position, getting myself up on my heels, and leaned back to brace myself with my hands. Curt then began hammering away at my pussy once more.

I now could see Courtney, who was on her hand and knees on the bench in front of the bed facing me. Brad was behind her pounding her vagina. I could tell she was getting close by the expression on her face. I watched as my girlfriend was fucked into a state of bliss by her partner.

After her orgasm I looked at her and said, "Wanna switch."

She smiled and nodded yes.

I dismounted Curt's cock and pulled Courtney onto the bed. She immediately mounted Curt and lowered her cunt onto his cock.

I laid on my back beside Curt and Courtney, and spread my legs offering my vacant hole for Brad's erection. He eagerly climbed up and filled my void. Our foursome fucked to the beat of the rap song that played. My ass milked Brads cock and I felt his pace quicken. I stopped him and pushed him free from my ass, as I wanted him to finish in my mouth. I rocked forward onto my knees and engulfed his rod with my mouth. I bobbed up and down on his cock tasting the combination of my ass and Courtney's pussy. Brad moaned and shot his load into my mouth. His creamy sperm I greedily lapped down, as I cleaned his beautiful penis.

Seconds later Curt exploded inside of Courtney's cunt. After the boys came they got dressed and exited the room leaving Courtney and I panting on the bed. Courtney's used pussy, had started to leak out Curt's seed onto the rubber sheets. Seeing this I positioned myself between her thighs, and licked at her swollen labia. I lapped up Curt's nectar and then crawled up Courtney's naked body and kissed her.

She smiled and kissed me back, "That was delicious, we have to do this more often."

We laid on the bed and recovered for a few minutes before gathering our clothes and exiting the room. Since the majority of the party had already left and most of our clothes were soaked in either pussy juice, sweat, or cum we didn't bother getting dressed and instead walked back to the main room, only wearing our skirts and high heels.

The last few couples exited, as we entered to find Steve, Greg, Laura, and Tara talking. The women were completely naked except for their high heels, and Laura's ripped stockings. Steve and Greg only wore shorts.

"There those two are," Laura exclaimed.

"We were beginning to think you had been kidnapped." Tara added.

Courtney and I just smiled and shared a laugh.

Greg looked at his watch and looked at Tara and Courtney, "Girls we should probably be heading home."

Tara quipped, "Like hell, we are still horny Greg."

Laura then chimed in, "Us girls are heading to the master. Once you boys get the help out the door come and join us."

Steve and Greg, agreed and set to helping the staff cleanup. Laura looked at Courtney and me and said, "Come on you two dirty sluts, follow us." Laura grabbed Tara and the two locked arms and strode off towards the master, as their naked asses bounced. Courtney and I followed suit of our mentor counterparts.

All four of us climbed into bed and made out for a while, as we waited for the boys. Greg and Steve finally joined us and they sat at the side of the bed. Laura then said, "Well Courtney and Jacki, me and Tara saved you guys a little present from Tyrone and the boys." They spread their legs to reveal their pussies were covered by those latex bandages that Laura had used before.

"How many loads tonight darling," Steve inquired

"I have 6 here," Laura answered as she tapped her mound, "Tara's little pussy only held 4."

"Now girls this surprise came directly from Tyrone and the boys, they said if we fed you all the black cum it would surely turn you into black cock sluts like us. I don't know about that but Tara and I just want our pussies eaten."

We crawled onto the bed together, Laura said to Courtney, "You come to me, Jacki you're with Tara."

I crawled myself in between Tara's thighs and positioned myself with my hands beneath her large ass. Tara then looked at me ordering, "Don't miss any darling," then removed her latex covering. Immediately her ravaged pussy began to gush and ooze with black semen. Tara grabbed my hair and slammed me face first into her used vagina. I lapped at the black seed that flowed from Tara as the boys stroked at their cocks. Steve quickly got hard and took positon behind Courtney preparing to stretch her with his massive erection. She squealed into Laura's ebony fucked pussy as Steve's girth stretched her tight pussy.

Greg was unable to get himself hard quick enough, and resorted to rimming, and finger fucking my ass. Laura saw this and dug into her night stand throwing him a large silicone dildo, and said, "Here Greg, fuck her with this." Greg obliged her requests, he quickly lubed the phallus and then began working it into my hole. The fake cock quickly slid into my rectum as I sucked at Tara's pussy. I finished cleaning her pussy of all it's cum, and then turned my attention towards her clit. Greg knew where to find my prostate, and used the plastic dick to fuck my spot.

I worked Tara into an orgasm, as I did she pressed my face harder against her button, and screamed, "Fuck, Fuck, Oh god yes," before squirting her juices into my pretty face.

Tara then pulled my head free, "Flip around and suck my husband's cock."

As I repositioned myself, I saw Steve was on his back while Courtney was riding his cock in reverse cowgirl. Laura had her face in-between their legs, licking at Courtney's pussy and Steve's shaft as they fucked.

Greg gave the sex toy to his wife, who resumed my fucking. I took Greg's soft penis into my mouth, and began to nurse his hardon back. I licked and sucked at his cock as it began to harden in mouth; meanwhile his wife worked the dildo in and out, removing it often to observe my gaping hole, which she would spit in before my ring closed. When Tara saw that I had worked Greg's cock back to full mast, she grabbed my hips and pulled me back off his cock and into her lap. She looked at her husband and his now hard cock, "Give her your cock baby, fuck her good." I scooted my ass forward resting my head on Tara's chest. Greg moved into position and lifted my legs so he had access to my ass. His swollen cock slid easily into my pussy and he slammed himself into me, bottoming out. He fucked me hard,the way he had fucked the boy on the couch from earlier.

I moaned and sighed, "Oh yes, Mr. Conner, fuck my pussy." Tara's rubbed my nipples and added encouragement for her husband, "Fuck her hard Greg, fuck her ass hard baby.

I looked to the other group in time to see Steve drive the full length of his cock into Courtney's cunt and deposit his load deep inside. The visual along with Greg's cock simulating my p-spot, sent me into orgasm and my muscle's squeezed his manhood as I came. Greg fucked my clenching anus harder as his breathing quickened. Tara could see he was close, and grabbed his head pulling his lips to hers. They shared a kiss, and then she ordered, "Breed this slut Greg." He gladly followed her demands, driving himself into me harder. Greg grunted and drove into me as he spilled his seed inside of me to the cheers of Courtney, Laura and Steve.

Greg held himself inside of me while he caught his breath as he began to soften, "Holy fuck, her ass is good."

Steve agreed, "Jacki's pussy is incredible, Courtney's was as well."

We all slept together in Steve and Laura's bed in a naked, sweaty, cum covered tangle.

The scent of sex lingered throughout the house, for over a week. I breathed it in reveling in the olfactory reminder of my cumming out party.

jacki697
jacki697
363 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
sissyboi69Aricsissyboi69Aricabout 2 years ago

My parties were never that good. What a great story. thank you

MisssissylisaMisssissylisaover 6 years ago
Please more!

There has to be more to this story to cum! I think every part has left me rock hard and bursting out of my knickers.

AnonymousAnonymousover 6 years ago
Please more

I really think that we need more

AnonymousAnonymousover 8 years ago
disappointed for my self

i'm feeling bad that i miss i missed an opportunity to become a girl. what a great story! not only the sex but seeing some one develop their selves and becomming what they feel inside. wow!

AnonymousAnonymousover 9 years ago
Awesome

Great series so far, loving Jacki's development and still feeling engaged in the narrative. Only feedback is to tighten up the grammar a bit. Phenomenal job overall though and looking forward to future releases!

Show More
Share this Story

Similar Stories

A College Sissy Ch. 01 Freshman is feminized, used by male roommate and girl.in Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Drink or Dare A drinking game with new friends changes everything.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
More Stories